The Catcher in the Rye is the ALLTIME Classic teen book. OK, Holden Caulfield is rich and negative. His time in New York is journey into maturity. Read it. Don't shoot anybody with the book in your pocket or I will revoke your library card!
"Choke" by Chuck Palahniuk. Funny, daring, and dark. Go along for the ride with Victor Mancini as he cruises sexual addiction recovery meetings for dates and fakes choking in restaurants to gain the help of strangers.